Process of



Patented July 24, 1928.

;,::RATENT .LOF ICE- HERMANN WAGNER; oFsonnmon 'rHE-TAo-nus, ilm) nsmz EICHWEDE-AND mun FISCHER; or ooHsr-oN-rirnmsnv, gnniaanmjassrenons ro GRASSELLI DYE- s'rurr CORPORATION, oannwyoitxnrt;A'coaroRArIoN ornnmiwnm.

PRbCESS. .OE; MIXED TEXTILE GOODS.

a. nmwingflap iicaaoa .iild was 28, 1926, Serial autism; giaiiff ia; Germany ret ial- 7, 1925..

It is already known that a number of pyrazolone azo dyestuffs possess a certain aflinity for the silkfibre.

when mixed with wool fibre, just as intensely as the wool fibre.

' ponent, or in both components simultaneously, one, or more carboxylic acid ester groups. The dyeings obtainable thereby,

which vary from yellow to orange, are dis tinguished by very good properties as to fastness. The wool and silk fibres are dyed even tints. Regarding the degree of the afiinity of the dyestufi's' for the silk fibre as compared with that for the wool fibre it should be considered that it is advantageous that the combinations of dyestuffs to be selected do not contain more acid groups, such as sulfoor free carboxylic groupsthan are necessary for rendering1 the 'dyestufi soluble in the usual dye bat.

The. following examples llustrate our invention:

(1) 1 kg. ofmaterial mixed ofr' wooland silk fibres is dyed in an appropriate manner in a dyebath containin g-2Ogr. of the dyephenyl-5-pyrazolone-3-carboxylic ethyl" ester,

while adding 10% of sodium sulfate and 4% of sulfuric acid. The dyeing thus obtained is not only distinguished for its great fastv 'ness but also for the fact that the woolas well as the silk fibres are dyed evenly and Lin an equal" shade. i

(2) By substituting for the dyestuffj'indicated in Exam le 1 an equal quantity of the dyestufi: ortho-aminobenzoic acid ethyl" ester'- 1--- 4'- sulfophenyl) 3 methyl- 5-.

pyrazolone, t ere is also obtained a very pure yellow dyeing, the silk fibre as well as the wool fibre belng dyed a tint of even shade and intensity.

. p (3) W'hen using the dyestufiz'm-aminobenzoic acid ethyl ester- 1-(4.-T-sulfo- However this aflinity is not sulficient to dye the silk fibre" esterfand operating thedyeingas, indicated .in Example 1: there are also obtained on the said'mate'rial very even tints.

The dyestufi' combinations specified in the foregoing examples are only to be regarded as representatives of the respective groups. They may, of course, be largely varied both in the diazo component and in the coupling I component.

Thus, for instance the pyrazolone compound mentioned in Examples'l and 3', may be replaced by the following combinations:

1) 1- (2- s'iilfophenyl) 5 pyrazolone 3- carboxylic acid ester.

(2) 1- (2'5-dichloro-4'-sulfophenyl) -5-pyrazolone-.3-carboxylic acid ester.

(3) l- (2'-chlor-5sul-fophenyl) -5-pyrazolone-3-carboxylic acid ester.

(4) 1- (2'-.methyl 6- chloro-' sulfophenyl)-5-pyrazolone-3-carboxylic acid ester.

(5) '1--(2- methyl 4fmethyl-5-sulfophenyl)-5-pyrazolone-3-carboxylic acid ester.

Furthermore in the. diazo component named in Example l the ortho-c'hloroaniline may for instance be replaced by: aniline, ortho-metaand ara-toluidine or the like.

However it is pre erable that the. diazo compounds do not contain any sulfo group, because ,inthis case the wool fibre is dyed more deeply thanthe silk fibre. In anycase, however, the dye'stulfs of this kind are distinguished from the analogous dyestuffs in which. the sulfotphenylpyrazolonecarboxylic acid is not esteri ed, by the property of dyeing the silk fibre in mixed material more deeply. W

For the pyrazolonesulfonic acid mentioned in Example 2 may be substituted any other sulfoaryl-3 methyl-5-pyrazolone but no sulfophenyl-5-pyrazolone-3-carboxylic acid.

In like manner, the diazo. compounds mentioned in Examples 2and 3 may be replaced by. any other aminoarylcarboxylic acid ester, for instance by 4-nitro-2-aminobenzoic acid methyl ester etc;

used to indicate the linkage of two components of an azod estufl'. Thus in the case of the dyestufi' o-c lor-anilinee 1- (4 sulfophenyl) -fi pyrazolone-ii-carboxylic ethyl ester the arrow indicates that fi-chlor-aniline has been diazotized and the diazo compound I It is to be understood that, in; the fore going description, the arrow ,is.

so formed has been coupled with the articular yrazolone compound stated. his use of tie arrow is described b Georgievics & Grandmougin, A Text-Boo of Dye Chemistry translated from the fourth German We claim; v

1. Process which comprises dyeing mlxed textile goods made of wool and sill: fibers with .a pyrezolone-ezodyestufi contain ng at least one carboxyl'ic acid ester group in the dyestufi' molecule, said pyrazolone-azo dye stufi conteining no free carboxylic acid edition by F. A. Mason, 1920, pages 87 and group linked to the carbon in the 3-position of the pyrazolone ring. w

2. As new products mixed wool and silk textile goods dyed with a pyrazolone-azo dyestufl containin at least one carboxylic acid ester group In the dyestuif molecule, said pyrazolone-azo, dyestufl containing no free carboxylic acid grou linked to the carbon in the 3-position of t e pyrazolone ring.

In testimony whereof, we aflix our signatures.

HERMANN WAGNER. HEINZ EICHWEDE. ERICH FISCHER; 

